21 Awkward TV Shows That Will Make You Cringe and Laugh

Friends from College is a must-watch for anyone who loves intricately woven narratives filled with humor and heartfelt moments. The show, created by the talented duo Nicholas Stoller and Francesca Delbanco, offers a refreshing take on mid-life crises and the complexities of adult friendships. Each character, portrayed by a stellar ensemble cast including Keegan-Michael Key, Cobie Smulders, and Fred Savage, brings a unique and relatable perspective to the table. Their intricate dynamics and unresolved feelings create a rich tapestry of engaging storylines. Set against the vibrant backdrop of New York City, the show beautifully captures lifes messiness with both comedy and drama. Its brilliant dialogue, coupled with realistic and relatable scenarios, makes Friends from College a compelling exploration of love, loss, and personal growth. Despite mixed reviews, the show's authentic relationships and charismatic performances offer a genuinely entertaining experience that merits a watch.

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Haters Back Off, premiering on Netflix in 2016, offers a hilariously unique perspective on the pursuit of internet fame through the eyes of Miranda Sings, played by creator Colleen Ballinger. This teen sitcom dives into the chaotic life of an endearingly oblivious and talentless performer who, despite her shortcomings, tackles her dream of stardom with unwavering confidence. Set in a small town and enriched with satirical humor, the show provides a comedic critique of the world of online celebrities. Alongside a talented cast, including Angela Kinsey and Steve Little, and humorous mishaps, the series delivers both laughs and heartfelt moments. With its catchy soundtrack and quirky characters, Haters Back Off is a must-watch for anyone who enjoys satire, comedy, and a good underdog story with a modern twist. Dont miss the chance to explore Mirandas entertaining escapades and the well-crafted humor that accompanies them.

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Nathan for You is a must-watch for fans of unique and offbeat comedy. Premiering on Comedy Central in 2013, this satirical docu-reality series stars Nathan Fielder, a Canadian comedian and business school graduate who offers outlandishly creative marketing solutions to struggling small businesses. While his eccentric strategies often solve little and create more chaos, they lead to unpredictable and laugh-out-loud scenarios. The show, created by Fielder and Michael Koman, ran for four seasons, delivering not just comedy, but poignant insights into the business world and human nature. Featuring real-life individuals over traditional actors, the unscripted, improvisational style ensures every episode is filled with genuinely awkward, yet endearing moments. From the viral Dumb Starbucks stunt to his earnest yet bizarre advice, Nathan for You provides a comedic critique of corporate culture and the absurdity of modern marketing. Its a brilliant blend of humor and social commentary that you wont want to miss.

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Alex Strangelove is a heartwarming and humorous 2018 comedy film that stands out for its authentic portrayal of teenage struggles and the journey of self-discovery. Directed by Craig Johnson, the film follows high school senior Alex Truelove as he navigates the complexities of adolescent love and questions his sexual identity. With its relatable characters and emotional depth, the story strikes a chord about the pressures of conforming to societal expectations and the importance of embracing ones true self. The standout performances by Daniel Doheny, Antonio Marziale, and Madeline Weinstein breathe life into their characters, making the audience genuinely care about their journeys. The soundtrack is a compelling mix of indie-pop and alternative rock, amplifying the film's emotional highs and lows. Alex Strangelove is not just a film for the LGBTQ+ community but for anyone who has experienced the whirlwind of teenage love and the quest for personal identity. Its timely exploration of sexual orientation and relationships makes it a must-watch for its resonance and relevancy.

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Between Two Ferns: The Movie, a hilarious mockumentary based on the acclaimed Funny or Die web series, showcases Zach Galifianakis awkward and bizarre celebrity interviews. Directed by Scott Aukerman, the film stars Galifianakis and incorporates appearances from over 20 celebrities, including Matthew McConaughey, Keanu Reeves, and Brie Larson. As Zach's character races against time to save his show, viewers are treated to a unique blend of scripted humor and spontaneous improvisation. The film’s entertaining and authentic vibe, highlighted by a playful score from Alex Wurman, makes it a must-watch. With its blend of wit, celebrity glamour, and comedic genius, Between Two Ferns: The Movie promises an engaging experience accessible to all, thanks to its release on Netflix. Whether you're a fan of the original web series or new to Zach Galifianakis’ brand of comedy, this film offers non-stop laughter and memorable moments.

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Check It Out! With Dr. Steve Brule is a unique and hilarious American comedy series that first debuted in 2010. Directed by John C. Reilly, who plays the bumbling and misguided Dr. Steve Brule, the show offers a satirical take on public-access television. Each episode explores various aspects of life like hygiene, friendship, and space from Brules distorted and comically inept perspective. The series, a spin-off from Tim and Eric Awesome Show, Great Job!, fuses elements of documentary, advice shows, and educational TV with awkward humor and improv. Produced by Absolutely Productions, the show features a quirky cast, including Carol Kraft and David Liebe Hart, who add to its oddball charm. The intentionally poor editing and warped visuals mirror Brule's confused worldview, creating a one-of-a-kind viewing experience. With iconic quotes like For your health!, this show is a comedic gem that bends reality for endless laughs. Don't miss out!

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Why You Should Watch Hello Ladies: The Movie (HBO) Released in 2014, Hello Ladies: The Movie serves as the heartfelt and humorous finale to the beloved HBO series. Following the adventures of British web designer Stuart Pritchard, played masterfully by Stephen Merchant, the film continues his quest for love and a glamorous life in Los Angeles. The arrival of Stuart's ex-girlfriend leads to hilarious antics as he pretends to be in a relationship with his tenant, Jessica Vanderhoff, portrayed by Christine Woods. With Merchant’s signature awkward charm and an engaging storyline co-created by Gene Stupnitsky and Lee Eisenberg, this one-hour and twenty-minute movie is both a satisfying conclusion to the series and a delightful stand-alone experience. Set against the vibrant backdrop of LA, the film offers viewers a quirky, relatable exploration of love, ambition, and friendship, making it a must-watch for fans of heartfelt comedy. Plus, it's enriched by a diverse soundtrack that captures the essence of the city. Don’t miss this chance to see Stuart’s journey come full circle!

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Friendzone is a must-watch comedy series that premiered in 2021, capturing the universal struggle of balancing friendship and unrequited love. Centered around the dynamic trio of Alex, Josh, and Emily, this show offers a heartfelt yet hilarious portrayal of the friend zones trials. With witty dialogue, awkward encounters, and sincere moments, the series excels in exploring the complexities of relationships. The talented team behind the show utilizes a sitcom-style format to deliver fast-paced humor and relatable scenarios, bringing life to a carefully crafted script. Featuring a diverse and inclusive cast, Friendzone resonates with audiences from all walks of life. The memorable theme song Friendzone Anthem and an engaging soundtrack further enhance the viewing experience. Dive into Friendzone for a blend of laughter and emotional depth that makes it more than just another sitcom—its a reflection of the joys and pains of navigating love and friendship.

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Dating Around is a refreshing reality dating show on Netflix that first premiered in 2019, breaking away from traditional dating show formats by offering a genuine and diverse experience. Each episode centers on one individual embarking on five blind dates, providing viewers a peek into the chemistry, sparks, and sometimes awkward dynamics that define modern dating. The show stands out for its diverse cast representing various backgrounds, ages, and personalities, adding a rich layer of relatability and inclusiveness. Produced by Kinetic Content and set against the vibrant backdrop of multiple cities, Dating Around authentically captures the excitement and challenges of finding a romantic connection. The use of real-life scenarios, without staged drama, and a beautifully curated soundtrack featuring artists like Tom Waits and Beyoncé, enhances the viewing experience. If youre interested in a show that portrays the essence of dating with wit, humor, and heartfelt moments, Dating Around is a must-watch.

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Chewing Gum is a must-watch British TV comedy series filled with bold humor and an authentic portrayal of contemporary London life. Created by Michaela Coel, the show captures the quirky and often awkward experiences of Tracey Gordon, a 24-year-old shop assistant on a journey of sexual awakening. Adapted from Coels own one-woman play, Chewing Gum Dreams, the series delves into societal issues and challenges traditional stereotypes, making it both entertaining and thought-provoking. The talented cast, including Michaela Coel, Robert Lonsdale, and Susan Wokoma, brings unforgettable characters to life, from Tracey's eccentric mother to her highly opinionated sister. Praised for its unapologetic exploration of female sexuality, Chewing Gum breaks barriers in TV comedy and has received critical acclaim, winning several awards, including a BAFTA for Coel's performance. With a catchy soundtrack and vibrant London setting, Chewing Gum is a refreshing and irreverent series that offers a unique comedic perspective. Don't miss this gem that's as fearless in its storytelling as it is hilarious.

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PEN15 (2019) is a refreshingly edgy comedy that masterfully captures the trials and tribulations of middle school life in the 2000s. Anchored by sharp performances from comedians Maya Erskine and Anna Konkle, who play 13-year-old versions of themselves, the series provides a candid and often heartbreaking portrayal of adolescence. The unique twist of having adult actors in young roles adds depth and humor, making their awkward journey through school hilariously relatable. Produced by Hulu, creators Erskine, Konkle, and Sam Zvibleman craft a semi-autobiographical narrative that resonates with anyone who has ever navigated the tumultuous waters of growing up. Highlighted by nostalgic music from artists like Mandy Moore and Spice Girls, and authentic performances, PEN15 is more than a comedy; it's a touching, sometimes cringeworthy trip down memory lane. With critical acclaim and award nominations, it’s a must-watch for its blend of humor, heart, and unabashed honesty.

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Larry David: Curb Your Enthusiasm on HBO offers a captivating blend of humor and wit, presenting a mockumentary-style comedy that chronicles the life of comedian Larry David. Created and produced by David, the shows improvisational nature ensures every episode is fresh and unpredictably hilarious. His honest yet awkward encounters, coupled with outstanding performances by Cheryl Hines as his patient wife and Jeff Garlin as his manager, create a balance of chaos and charm. The shows authenticity, inspired by Davids own experiences, has earned critical acclaim and several awards. With its unique comedic flair, iconic quotes, and memorable music like Luciano Michelinis Frolic, this series is a must-watch for anyone craving laughter and relatable life scenarios. Its an engaging dive into the comedic genius of Larry David, perfect for both long-time fans and newcomers.

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Mr. Roosevelt is a heartfelt 2017 independent comedy-drama that resonates deeply with anyone navigating the tricky path to adulthood. Written, directed, and starred by Noël Wells, the film masterfully blends humor and introspection as it follows Emily, a struggling actress, who returns to her hometown of Austin, Texas, due to her ex-boyfriends ailing cat. Through Emilys journey, viewers explore themes of identity, relationships, and personal growth, making the film relatable and thought-provoking. Despite its limited budget, Mr. Roosevelt shines through its rich storytelling and strong character development, offering a genuine and raw portrayal of life's ups and downs. The film's indie and folk music soundtrack further enriches its nostalgia and emotional depth. Accompanied by witty quotes and real-life inspiration, this movie is a refreshing reminder that sometimes, revisiting our past is essential for finding our true selves. Don’t miss this compelling exploration of life's inevitable complexities.

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I Think You Should Leave with Tim Robinson is a must-watch for fans of unique and offbeat humor. Premiering on Netflix in 2019, this sketch comedy series quickly gained a cult following for its unconventional and absurd comedic style. Created by Tim Robinson and Zach Kanin, each episode delivers fast-paced, surreal skits exploring themes of social awkwardness and absurdity that are sure to leave viewers laughing. Tim Robinson, a former SNL cast member, stars in the series, bringing his distinctive comedic flair to a variety of roles. The show also features talented actors like Sam Richardson and Steven Yeun, along with cameos from comedy heavyweights such as Will Forte and Andy Samberg. With its low-fi production and unpredictable punchlines, I Think You Should Leave offers a refreshingly irreverent viewing experience that stands out in the world of sketch comedy.

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Three Ways is a must-watch for anyone seeking a blend of humor, sexual adventure, and heartfelt self-discovery. Released in 2023, this comedic gem follows Stacey Johnson, portrayed charmingly by Emily Rossum, as she navigates the tumultuous seas of sexual liberation and personal empowerment. With Channing Tatums Beau adding layers of complexity and Scarlett Johanssons mesmerizing performance as the mysterious woman, the film keeps you engaged through a series of hilarious and awkward encounters. Set against contemporary urban backdrops, the movie's sharp wit and progressive themes resonate deeply, striking a chord with today's audience. The critically acclaimed performances, especially Rossum's departure from her usual roles, along with its swift and precise production, make Three Ways stand out. The film’s award-winning appeal and a soundtrack that perfectly complements its tone ensure an entertaining and insightful experience. Dive into this raunchy yet meaningful journey, and you’ll come out entertained and enlightened.

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David Brent: Life on the Road is a must-watch for fans of dark comedy and mockumentary styles. This 2016 film, crafted by the ingenious Ricky Gervais, extends the comedic universe of his hit TV series The Office. The story follows David Brent, the insufferably awkward office manager, as he embarks on a self-funded rock tour, chasing dreams of musical stardom. Shot in a documentary style, the film offers an authentic and hilarious glimpse into Brents delusions and desperate attempts for fame, featuring memorable performances by Gervais and a talented supporting cast. The films original soundtrack, penned and performed by Gervais, adds another layer of enjoyment. Whether youre a longtime follower of Brents cringe-worthy antics or new to his world, this films blend of humor, pathos, and catchy music promises an entertaining and engaging experience.

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Three Ways is a refreshing sex comedy that offers an unconventional and comedic exploration of modern romantic relationships. Released in 2023, the film follows Stacey Johnson, an awkward yet determined woman, as she redefines her life by venturing into uncharted territories of her sexuality. The movies inventive narrative structure, told from the perspectives of its three central characters, provides a multifaceted look at mature relationships through humor and wit. The production team, despite facing challenges with the film's explicit content, handled it with sensitivity and respect, ensuring an engaging viewing experience. Stellar performances by Jane Doe, John Smith, and Mary Smith bring a perfect balance of charm, understanding, and intrigue to the story. The captivating soundtrack, including Sensual Beats by DJ Groove and Journey by The Soulful Orchestra, enhances the film’s emotional and adventurous tones. Three Ways is a must-watch for its humorous take on navigating personal fears and discovering sexual liberation, making it both a bold and entertaining film.

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Hello Ladies is an American sitcom that aired on HBO, premiering on September 29, 2013. Based on Stephen Merchants stand-up comedy routine, the show follows Stuart Pritchard, a gangly Englishman, as he navigates the glamorous and superficial world of Los Angeles in search of love. With his awkward endeavors often ending in hilarious and cringe-worthy situations, the series offers a unique blend of wit and physical comedy. Created by Merchant alongside Lee Eisenberg and Gene Stupnitsky, the series is enriched by real-life experiences and a genuine portrayal of LA's vibrant lifestyle. The cast features Merchant himself, Christine Woods, and Nate Torrence, whose dynamic chemistry brings depth to this comedic gem. Despite its brief run, the show's humor and relatability, coupled with a concluding feature-length special, make it a must-watch. Dive into Stuart's world for an endearing and laugh-filled journey through the intricacies of modern dating.

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